Physical isolation of these two states is the most secure. In other words, don't do clearnet and Tor shit on the same computer. Are you using random wifi hotspots? Otherwise this is irrelevant. MAC addresses are not broadcast over the internet. Only devices physically linked to your dongle know its MAC address. If you're paying for internet service, they still know your identity. If you are connecting directly from home, they know your identity. Excellent choice! Finally people are getting the importance of FDE. Don't forget to disable the microphone, too. Good choice, although lately I've come to the conclusion that an anonymizing middle box is the safest setup. It's a physical device, like a computer in an HTPC form factor, with 2 network interface cards, that sits between your main computer and your home router (let the router be the gateway to the public internet, not the anon middle box). It runs a stripped down Linux or BSD variant with Tor, and transparently proxies all connections over Tor. It's basically Whonix with the Gateway on a separate physical device. Don't get me wrong, your setup is orders of magnitude safer than most, but a gateway on a separate device is safer still. VPNs are good for certain use cases, but I've never understood the need to pay with bitcoin. If you connect to the VPN server directly, they know your IP address. LE can deanonymize you if the VPN provider cooperates. I suppose if you live with a bunch of other people, you have some plausible deniability. Superficially that seems safe, but don't you think you stand out as being "a weird (presumably young) guy who does nothing of value on the internet?" I think it's safer to maintain two identities. Have one computer with Windows, unencrypted, nothing sensitive. Act normal, have a Facebook/Twitter account, buy shit online, look just like everyone else. On the side (on separate physical devices), you do your dirty work. I don't know, though. I'm not too familiar with research on social profiling of criminal activity. Sounds good. Just don't use TorChat. That makes you a hidden service which opens you up to new attacks. Run Pidgin over Tor and connect to a separate XMPP server. Not sure why you're having problems. Printer support on Linux is pretty good these days. Check out http://www.linuxfoundation.org/collaborate/workgroups/openprinting/database/databaseintro